1,3-diphenyl-2-azaanthracene and 8-aza-7-phenylbenzo[a]fluoranthene in the diene synthesis

The diene condensation of 1,3-diphenyl-2-azaanthracene with maleic anhydride proceeds under more severe conditions than the analogous condensation with anthracene. On the basis of an analysis of the PMR data for the adduct obtained it was assumed that isomers of α,α′-[9,10-dihydro-2-aza-1,3-diphenylanthrylene(9,10)]succinic anhydride with respect to the position of the anhydride bridge relative to the pyridine ring are formed in this condensation. 9,10-Dihydro-2-aza-1,3-diphenyl-9, 10-(1′-cyanoethylene)anthracene was obtained in the condensation of the same azaanthracene with acrylonitrile. α,α′-[5H-8-Aza-7-phenylbenzo[a]fluoranthrylene (5,12b) ]succinic anhydride is formed as a result of the similar condensation of 8-aza-7-phenylbenzo[a]fluoranthene with maleic anhydride, while isomeric (with respect to the position of the nitrile group in the ethylene bridge) 5H-8-aza-7-phenyl-5,12b-(cyanoethylene)benzo[a]fluoranthenes were isolated in its condensation with the acrylonitrile. Data from the PMR and IR spectra were used to prove the structures of the adducts of the diene synthesis obtained. © 1981 Plenum Publishing Corporation.